Potassium Bromide → N,N-bis(1H-benzimidazol-2-ylmethyl)-N-phenylamine chromium (III) chloride

HRID 1645209Notes

Reaction equation

HRID 1645209 reaction equation
[Cl-:1].[Cr+3:2].N1C2C=CC=CC=2N=C1CNCC1NC2C=CC=CC=2N=1.[Cl-].[Cl-].[NH:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[CH2:35][N:36]([CH2:43][C:44]1[NH:48][C:47]2[CH:49]=[CH:50][CH:51]=[CH:52][C:46]=2[N:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[K+].[Br-]>CN(C=O)C>[Cl-:1].[Cr+3:2].[NH:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[CH2:35][N:36]([CH2:43][C:44]1[NH:45][C:46]2[CH:52]=[CH:51][CH:50]=[CH:49][C:47]=2[N:48]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1.[Cl-:1].[Cl-:1]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 66775276N,N-bis(1H-benzimidazol-2-ylmethyl)-N-phenylamineHCID 86638460N,N-bis(1H-benzimidazol-2-ylmethyl)amine chromium (III) chloride

Product 1

HCID 86638465N,N-bis(1H-benzimidazol-2-ylmethyl)-N-phenylamine chromium (III) chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3h was synthesised by an analogous procedure to that described for 3a using N,N-bis(1H-benzimidazol-2-ylmethyl)-N-phenylamine (0.20 g, 0.56 mmol) and CrCl3(THF)3 (0.21 g, 0.56 mmol). Yield 0.23 g (87%). Anal. Calc. for C22H19Cl3CrN5 (in %): C, 51.63; H, 3.74; N, 13.68. Found C, 51.49; H, 4.95; N, 13.58. IR (KBr, cm−1), υ 3224 (NH, s), υ 1637-1540 (ArC═C, C═N, m), δ 1454, 1477, 1498 (N—H, s, m), υ 1275 (CN, s), δ 748 (CH, s). UV-VIS (DMF, 298 K): λmax/nm=484, 678, 707 (shoulder). +FAB-MS: (m/z): 475 ([M-Cl]+), δ 440 ([M-2Cl]), 354 ([M-CrCl3]+). μeff·=3.95 MB.

Sources & evidence

ORD record
ord-af434b7ae4064b88ab9fb6e122afbb9b
Source dataset
uspto-grants-2012_02
Patent number
US08124698B2

Reaction notes

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